6-Amino-1-methyl-5-nitrosouracil → HCID 178481641, compound

Participants

Reaction Conditions

Reaction Steps

To a suspersion of 2.42 g (14.3 mmol) of the 6-amino-1-methyl-5-nitrosouracil in water heated to 90° C., was added 30 mL of a 38% solution of NaHSO3 over 10 minutes and the reaction allowed to continue until the reaction mixture was completely decolourized. After cooling the reaction mixture to 0° C., 5,6-diamino-1-methyluracil crystallized from the medium. After filtering off, washing with water, ethanol and diethylether and drying 2.14 g (80%) of the intermediate 5,6-diamino-1-methyluracil was isolated. 8.71 g (55.8 mmol) of 5,6-diamino-1-methyluracil was dissolved in 100 mL water and 50 mL acetic acid upon heating. After cooling to room temperature, a solution of 3.86 g (55.9 mmol) NaNO2 in 17 mL water was added over 5 minutes. The mixture was stirred for 5 minutes and then refluxed for a short time. After standing for two days at room temperature, 3-methyl-8-aza-9H-xanthine crystallized from the mixture. After filtering off, drying, recrystallization from water/ethanol 1:1 and drying 3.57 g (38%) of 3-methyl-8-aza-9H-xanthine was obtained (m.p. 313–320° C.).

Provenance & Evidence